The trans-1-chloro-3,3,3-trifluoropropene (abbreviated designation: 1233zd(E)) is a compound useful as a next-generation polyurethane foaming agent, working fluid, refrigerant and the like which have low global warming potentials (GWP).
Usually, 1-chloro-3,3,3-trifluoropropene (abbreviated designation: 1233zd) is produced using a fluorinating catalyst by fluorinating 1,1,1,3,3-pentachloropropane (abbreviated designation: 240fa) with hydrogen fluoride or by fluorinating 1,1,3,3-tetrachloro-2-propene (abbreviated designation: 1230za) with hydrogen fluoride. This fluorination is conducted as a gas-phase or liquid-phase reaction, and the liquid-phase reaction is conducted under pressure.
For example, Japanese Patent Application Laid-Open No. H9-183740 describes a method for obtaining 1-chloro-3,3,3-trifluoropropene (1233zd) by reacting 1,1,1,3,3-pentachloropropane (240fa) with hydrogen fluoride in the presence of a fluorinating solid catalyst in a gas phase. Japanese Patent Application Laid-Open No. H11-180908 describes a method for obtaining 1-chloro-3,3,3-trifluoropropene (1233zd) by a catalyst-free reaction of 1,1,1,3,3-pentachloropropane (240fa) with hydrogen fluoride. Japanese Unexamined Patent Application Publication (Translation of PCT Application) No. 2007-501843 describes a method for producing 1-chloro-3,3,3-trifluoropropene (1233zd) by reaction of 1,1,1,3,3-pentachloropropane (240fa) in a reaction vessel in the presence of Lewis acid catalyst or Lewis acid catalyst mixture at a temperature below 150° C. in a liquid phase, continuous recovery of hydrogen chloride and 1-chloro-3,3,3-trifluoropropene (1233zd) generated in the reaction vessel, and isolation of 1-chloro-3,3,3-trifluoropropene (1233zd) obtained in the previous step.
When reacting 1,1,1,3,3-pentachloropropane (240fa) with hydrogen fluoride to obtain 1-chloro-3,3,3-trifluoropropene (1233zd), an equilibrated reaction under the influence of the partial pressures of hydrogen fluoride and hydrogen chloride is established, and the reaction product contains, in addition to 1-chloro-3,3,3-trifluoropropene (1233zd), a more intensively fluorinated product such as 1,1,1,3,3-pentafluoropropane (abbreviated designation: 245fa) and the like, or a product having a lower fluorination degree such as 1,1,3,3-tetrachloro-1-fluoropropane (abbreviated designation: 241fa), 1,3,3-trichloro-1,1-difluoropropane (abbreviated designation: 242fa) and the like. 1,3,3-trichloro-1,1-difluoropropane (242fa), which is present as an intermediate product in a catalyst-free liquid-phase fluorination reaction for producing 1233zd from 240fa, is problematic especially because it reduces the productivity due to its accumulation in a reaction vessel as a result of its extremely low fluorinating reaction rate.
Japanese Patent Application Laid-Open No. H9-183740 employs a solid fluorinating catalyst, which should be watched to avoid inactivation and also should be packed again.
Japanese Patent Application Laid-Open No. H11-180908 employs 240fa to produce 1233zd and/or 1,3,3,3-tetrafluoropropene (abbreviated designation: 1234ze) by a catalyst-free gas-phase fluorinating reaction, which requires a prolonged heating at a high temperature.